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How to Wear Loafers, According to a Shoe-Obsessed Fashion Editor
If there’s one pair of shoes that has truly stood the test of time in my closet, it’s loafers. I first started wearing them in my corporate America days–back when a button-down shirt and blazer were basically my daily uniform. Fast forward 15+ years and loafers are still the shoe I reach for most. They’ve outlasted trendy sneakers, a rotating collection of boots, and even a fling with ballet flats. Why? Because loafers strike that perfect balance of classic and versatile.
Whether you lean preppy, minimalist, or like a little edge, loafers just work. They can be polished for business casual, laid-back with denim, or unexpectedly chic with a skirt. Consider this my love letter to loafers–and all the ways I style them.
Loafers with a Midi Dress
There’s something so effortless about pairing loafers with a midi dress. A flowy dress and structured loafer balance each other beautifully–the softness of fabric against the sturdiness of leather. Sleek leather loafers like these are typically my go-to here, especially if I’m adding a belt or cardigan for polish. A pair of penny loafers keeps the vibe timeless, but chunky loafers can also add an on-trend edge.
Loafers with Literally Anything
I’m not exaggerating when I say loafers go with literally anything. Jeans, trousers, mini skirts, shorts, stirrup leggings–you name it. The trick is choosing the right loafer for the outfit. Tassel loafers for a classic prep look, suede loafers for texture, chunky loafers when you want a little fashion-girl energy, or sleek brown loafers when you’re keeping things understated. These loafers combine the brown, suede, and tassels – so yes, I’m obsessed. Consider them the “chameleon shoe” in your wardrobe.
Loafers with Sweats
Yes, sweats. The combo sounds wrong but feels so right. A slouchy pair of joggers that flatter like these, a fitted tee or white button-down shirt, and loafers instantly transform “I just left the gym” into “off-duty chic.” Think of it as the elevated version of sneakers with loungewear. Add a trench coat or blazer on top and suddenly your sweats are part of an actual outfit.
Loafers with Jeans + Cardigan + Button Down
This is my signature outfit formula. Straight-leg jeans, a crisp button-down shirt, a cozy cardigan layered on top, and loafers at the ankle–it doesn’t get more classic. It works year-round, from black leather or chunky loafers in fall to suede loafers in spring (I’m wearing the Madewell suede penny loafers in the photos above). Swap the cardigan for a blazer and you’ve got instant business casual.
Loafers with Trousers + Blazer
Speaking of business casual–loafers and trousers with a blazer will never not feel timeless. This is the outfit that first hooked me on loafers. A structured jacket, pleated trousers, and a pair of burgundy or black leather loafers like these? Perfection. Bonus points if you let your loafers add a pop of color or interesting texture (think patent, suede, or even white).
Loafers with Socks
One of my favorite styling tricks: socks with loafers. It gives your outfit a slightly fun, retro vibe while also being practical. White crew socks (I love these socks with the ruffle on top) with black loafers and denim? Classic. Sheer or lacy socks peeking out from chunky loafers? Fashion-forward. Don’t be afraid to play with color either–burgundy loafers with a contrasting sock can totally change the outfit’s mood. Here are the do’s and don’ts of wearing socks with loafers.
Loafers with a Mini Skirt
Loafers and mini skirts are a match made in preppy heaven. It’s very “back-to-school” in the best way. Pair a plaid mini like this with a sweater and penny loafers (once again, I recommend these loafers from Madewell), or keep it sleek with a solid mini, fitted tee, and chunky loafers. If you’re hesitant about bare legs, add tights for an extra polished finish.
Loafers with Stirrup Leggings
This is one of those styling hacks that feels like it shouldn’t work, but it does. Stirrup leggings, especially black ones, tuck seamlessly into loafers. Add a button-down shirt layered under a sweater and you’ve got an outfit that feels fresh but still classic. Think of it as the modern answer to skinny jeans with flats.
Loafers with Shorts
When warm weather hits, don’t push your loafers to the back of the closet. Pair them with tailored shorts (these are my favorite) and a crisp shirt for a business-casual summer or warm fall look, or with denim cutoffs and a trench coat for weekend errands. Loafers with shorts add that unexpected polish that sneakers just can’t replicate.
The Best Loafers for Women
If you’re building your loafer collection, here are the pairs worth considering:
Invest in at least one pair of cognac leather loafers (I recommend these) –you’ll wear them more than you think. From there, add variety with suede, tassels, or a pop of color.
Final Thoughts
Loafers are more than just a shoe–they’re a style philosophy. They prove that you don’t have to sacrifice comfort for polish, or timelessness for trend. They’re the one piece of footwear that will carry you from business casual meetings to weekend errands to date night without missing a beat.
So yes, I’ve owned loafers for over 15 years–and I’m still just as in love. If you’re building a wardrobe that’s both classic and versatile, start with a pair of loafers. Trust me, they’ll become the shoe you reach for more than anything else.
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